HCID 19388936, compound → HCID 19389083, compound

HRID 1110314Notes

Reaction equation

HRID 1110314 reaction equation
[C:1]([CH2:4][N:5]([C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[C:26]([O:31]CC2C=CC=CC=2)[C:25]([O:39]CC2C=CC=CC=2)=[CH:24]3)[CH:13]=[C:12]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8])([OH:3])=[O:2]>[Pd].C1COCC1>[C:7]([CH2:6][N:5]([C:10]1[CH:11]=[C:12]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH:13]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[C:26]([OH:31])[C:25]([OH:39])=[CH:24]3)[CH:15]=1)[CH2:4][C:1]([OH:3])=[O:2])([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 19388936HCID 19388936, compound

Product 1

HCID 19389083HCID 19389083, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.16 g of N-(carboxymethyl)-N-[3-(octadecyloxy)-5-[4-[2,3-bis(phenylmethoxy)-6-naphthalenyl]butoxy]phenyl]glycine and 0.35 g of 10% palladium on carbon in 75 ml of THF was stirred under a hydrogen atmosphere until uptake ceased after 6 hours. The catalyst was removed by filtration through a Celite pad and the filtrate was concentrated to a solid which was triturated with hexane and filtered to give 0.835 g (90% yield, mp 153°-155°) of N-(carboxymethyl)-N-[3-[4-(2,3-dihydroxy-6-naphthalenyl)butoxy]-5-(octadecyloxy)phenyl]glycine.

Workup

  1. customThe catalyst was removed by filtration through a Celite pad
  2. concentrationthe filtrate was concentrated to a solid which
  3. customwas triturated with hexane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-127a93c6742149eba29486a742d3ef38
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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